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OChem Blows
Organic Chemistry Blows Goat
| Question | Answer |
|---|---|
| Hydroxide ion removes a proton from alpha-Carbon of the keto tautomer, forming enolate ion. Enolate ion has two resonance contributors. Protonation on oxygen forms enol tautomer, but protonation on alpha-carbon yields keto tautomer. | Base-Catalyzed Keto-Enol Interconversion |
| The acid protonates the carbonyl oxygen of keto tautomer. Water removes a proton from the alpha-carbon, forming the enol tautomer. | Acid-Catalyzed Keto-Enol Conversion |
| A base removes a proton from the alpha-carbon, forming an enolate in. The enolate ion reacts with an electrophile. | Base-Catalyzed Alpha-Substitution |
| The acid protonates the oxygen, the most electron-dense atom in the molecule. Water removes a proton from the alpha-carbon. The enol reacts with an electrophile. | Acid-Catalyzed Alpha-Substitution |
| The carbonyl oxygen is protonated. Water removes a proton from the alpha-carbon, forming an enol. The enol reacts with an electrophilic halogen. The very acidic protonated carbonyl group loses a proton. | Acid-Catalyzed Halogenation |
| The hydroxide ion removes a proton from the alpha-carbon, forming an enolate ion. The enolate ion reacts with the electrophilic halogen. | Base-Promoted Halogenation |
| All of the hydrogens of the methyl group are replaced by halogens. The product is a trihalo-substituted ketone. Hydroxide ion attacks carbonyl carbon of trihalo-substituted ketone. Transfer of a proton forms carboxylate ion and iodoform. | Haloform Reaction |
| PBr3 converts the carboxylic acid into an acyl bromide. The acyl bromide is in equilibrium with its enol. Bromination of the enol forms the alpha-brominated acyl bromide, which is hydrolyzed to the alpha-brominated carboxylic acid | Hell-Volhard-Zelinski Reaction |
| A base removes a proton from the alpha-carbon of the carbon acid. The enolate ion adds to the beta-carbon of an alpha,beta-unsaturated carbonyl compound. The alpha-carbon is protonated. | Michael Reaction |
| A base removes a proton from the alpha-carbon, creating an enolate ion. The enolate ion adds to the carbonyl carbon of a second molecule of the carbonyl compound. The negatively charged oxygen is protonated. | Aldol Addition |
| A base removes a proton from the alpha-carbon, forming an enolate ion. The enolate ion eliminates the OH group, which picks up a proton as it leaves to make it a better leaving group. | E1cB reaction |
| A base removes a proton from alpha-carbon, creating an enolate ion. The enolate ion adds to the carbonyl carbon of a second molecule of the carbonyl compound. The pi bond reforms, eliminating an alkoxide ion. | Claisen Condensation |
| A base removes a proton from the alpha-carbon, creating an enolate ion. The enolate ion adds to a carbonyl carbon. The pi bond reforms, eliminating an alkoxide ion. | Dieckmann Condensation |
| The first stage is a Michael reaction that forms a 1,5-diketone. The second stage is intramolecular aldol addition. Heating the basic solution dehydrates the alcohol. | Robinson Annulation |
| A proton is easily removed from alpha-carbon because it's flanked by 2 ester groups. Resulting alpha-carbanion reacts with alkyl halide, forming alpha-substituted malonic ester. | Malonic Ester Synthesis |
| Heating alpha-substituted malonic ester in acidic aqueous solution hydrolyzes both ester groups to carboxylic acid groups, forming alpha-substituted malonic acid. Further heating decarboxylates 3-oxocarboxylic acid | Decarboxylating carboxylic acids |
| The alcohol displaces the chloride ion from the dimethylchlorosulfonium ion in an Sn2 reaction. The product of the first step loses a proton. An E2 reaction forms the aldehyde (or the ketone). | Swern Oxidation |
| The ketone and the peroxyacid form an unstable tetrahedral intermediate with a weak O-O bond. As the O-O bond breaks heterolytically, one of the alkyl groups migrates to oxygen. Similar to 1,2-shifts | Baeyer-Villiger Oxidation |
| OsO4 forms a cylic intermediate when it reacts with an alkene. Its a syn addition because both oxygens are delivered to same side of double bond. Intermediate is hydrolyzed with aqueous hydrogen peroxide. H2O2 reoxidizes reagent back to OsO4 | Cis-Glycol Formation |
| An elecrophile adds to one of the sp2 carbons and nucleophile adds to the other. E+ at oxygen at one end of ozone w/ nucleophile at other end. Molozonide product is unstable due to two O-O bonds, immediately rearranges to more stable ozonide | Ozonide Formation |
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